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Meet Katherine Sherbrooke of Fill the Sky, Hemingway House and GrubStreet

Today we’d like to introduce you to Katherine Sherbrooke.

Katherine, can you briefly walk us through your story – how you started and how you got to where you are today.
My dream as a kid had always been to write fiction. I was an avid reader and found books to be magical. I worked hard on my writing, majored in English at Dartmouth, wrote my senior thesis on F. Scott Fitzgerald, and then set about to find my way in the world. I ended up landing a job at Inc. Magazine and was surprised to find myself enthralled by the start-up stories that were featured in the magazine. I particularly admired the entrepreneurs who were willing to break “corporate” rules and create customer and employee centered businesses that cared deeply about being great places to work. Having caught the entrepreneurial bug, but with no business training whatsoever, I went out to Stanford to get my MBA. When I returned to Boston, I co-founded Circles, a marketing services company, with a classmate from Stanford. Fast forward twelve years or so, after growing the company to about $65 million in revenue, Circles was acquired by a large multinational company. I stayed on for two years post-acquisition, but then decided it was time for a break. I assumed I would take a little time off and then start up another company. Through a series of events, however, I began to “remember” that long held dream of writing fiction. But I had no idea where to start. Luckily, I discovered GrubStreet, a creative writing organization in Boston (and in fact the largest organization of its kind in the country). GrubStreet quickly became my lifeline on everything from learning craft to understanding the publishing industry, and perhaps most important of all, finding a community of aspiring authors that support and cheer each other on through the crazy process of trying to create art. Through GrubStreet I learned that fiction is more than just magic– it is a craft that can be studied, practiced and improved. I also learned that getting a novel published is no easy feat. I had always assumed that all worthy novels find a place on the bookstore shelf, but I quickly learned that getting a book published requires finding just the right publisher at just the right time who is looking for just the kind of story you have been laboring over for three or five or ten years. It’s a needle-in-the-haystack exercise if ever there was one. My first novel, Fill the Sky, is about three life-long friends who travel to Ecuador in hopes that shamans there can save one of them from cancer. It was lucky enough to find a home at SixOneSeven Books, a small publisher in Boston. The book came out in the fall of 2016, and I finally joined the ranks of published authors– a long winding road to a childhood dream come true!

Overall, has it been relatively smooth? If not, what were some of the struggles along the way?
Creating something from nothing is a scary business. My co-founder used to say (and I don’t know who to credit the original quote to…) “there is a fine line between an entrepreneur and a madman. They both see things that aren’t there.” Writing a novel and starting a business share that in common. You have something in your head and you hope that if you put the pieces together just right, it will become something of value. But there are always legions of detractors along the way, including your own interior voice telling you your idea, your skills, your talent just aren’t good enough. In the case of writing, I believe the creation of art comes from somewhere deep inside, a place far more personal than the logical business “brain” if you will, and so putting it out there to the world can feel very risky. Having it not be “accepted” (whether in the form of praise during a workshop session or when trying to find an agent or publisher) can be devastating. In both cases, there were stops and starts along the way, obstacles that seemed enormous in the windshield, but then thankfully shrunk away in the rear-view mirror. Perseverance is the thing that I suppose kept me moving forward through it all.

Fill the Sky (book), Hemingway House (writer’s retreat), and GrubStreet (creative writing center) – what should we know? What do you guys do best? What sets you apart from the competition?
I’d like to talk about GrubStreet here, as I am currently the Chair of the Board– grateful that I can use my business brain to help this amazing organization in any way I can. At the core of GrubStreet, founded 20 years ago by Eve Bridburg, is the belief that creative writing increases empathy and builds bridges– between people, within communities, across race, religion, national boundaries, dissolving what separates us by allowing us to experience, if even only on the page, someone else’s situation. Brain science has actually recently proven this idea. When you are entirely transported by a story, your brain actually believes you are living it. But that level of “transporting,” if you will, only happens through a well-crafted story. So GrubStreet helps writers, at every level, rigorously improve their craft in a loving atmosphere that is supportive and encouraging. And GrubStreet is particularly committed to encouraging voices previously unheard and helping unearth stories previously untold, building bridges to uncharted, or misunderstood or underrepresented territory. We are also committed to ensuring that anyone interested in this process be able to participate, regardless of ability to pay– no small feat for what started as a tiny non-profit. We are very proud of our scholarship program which has helped hundreds of writers improve their craft. Our next step, which we hope will come to reality in the not-too-distant future, is to create the first integrated Narrative Arts Center in Boston, a place where on top of our dynamic curriculum of craft and publishing classes, we will have a bookstore, gathering spaces for readers and writers, and a stage and event space where the written word can be performed and where book launches and readings can take place—a welcoming “store front” for Bostonians and visitors alike to experience the power and beauty of the written word.

What is “success” or “successful” for you?
As for my writing, I see art as a handshake. As much as my story can exist within the pages of a book, it doesn’t really come to life until it is experienced by another person. It doesn’t really exist until the imagination of the reader brings it to life. I suppose that’s the real magic of the medium. So success to me in that realm is to know that the story touched the reader in some way, transported them, if even for a moment, and ideally helped them understand something that they hadn’t before.

Contact Info:

Image Credit:
(From top) Katherine with her novel; with two friends at a book party in Portland, OR; with her book group; a promo shot for the audio book; with another book group (she loves to join groups of readers to discuss the novel); and with her two sons.

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